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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 00:55:22 UTC

Update Date

2023-02-21 17:29:53 UTC

HMDB ID

HMDB0060346

Secondary Accession Numbers

HMDB60346

Metabolite Identification

Common Name

2-Chloro-5-methylmaleylacetate

Description

2-Chloro-5-methylmaleylacetate belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. 2-Chloro-5-methylmaleylacetate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Chloro-5-methylmaleylacetate exists in all living organisms, ranging from bacteria to humans. These are keto acids with a 6 to 12 carbon atoms long side chain.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0      -0.770   1.334   0.000  0.00  0.00          Cl+0
HETATM    9  O   UNK     0       1.540  -2.667   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       6.160  -2.667   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.850  -4.001   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -2.310  -1.334   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4    5                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2    7    8                                                  
CONECT    5    2    3    9                                                  
CONECT    6    3   10   11                                                  
CONECT    7    4   12   13                                                  
CONECT    8    4                                                            
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Chloro-5-methylmaleylacetic acid	Generator
(2E)-2-Chloro-5-methyl-4-oxohex-2-enedioate	Generator

Chemical Formula

C₇H₇ClO₅

Average Molecular Weight

206.58

Monoisotopic Molecular Weight

205.998201041

IUPAC Name

(2E)-2-chloro-5-methyl-4-oxohex-2-enedioic acid

Traditional Name

(2E)-2-chloro-5-methyl-4-oxohex-2-enedioic acid

CAS Registry Number

Not Available

SMILES

CC(C(O)=O)C(=O)\C=C(\Cl)C(O)=O

InChI Identifier

InChI=1S/C7H7ClO5/c1-3(6(10)11)5(9)2-4(8)7(12)13/h2-3H,1H3,(H,10,11)(H,12,13)/b4-2+

InChI Key

KECVAQLNZFMLLN-DUXPYHPUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents

Substituents

Medium-chain keto acid
Halogenated fatty acid
Branched fatty acid
Methyl-branched fatty acid
Beta-keto acid
B'-hydroxy-alpha,beta-unsaturated-ketone
Unsaturated fatty acid
Dicarboxylic acid or derivatives
1,3-dicarbonyl compound
Fatty acyl
Beta-hydroxy ketone
Alpha-halocarboxylic acid or derivatives
Alpha-halocarboxylic acid
Enone
Alpha,beta-unsaturated ketone
Acryloyl-group
Vinylogous halide
Ketone
Chloroalkene
Haloalkene
Vinyl halide
Carboxylic acid derivative
Carboxylic acid
Vinyl chloride
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organochloride
Organohalogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

oxo carboxylic acid (CHEBI:81656 )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.47 g/L	ALOGPS
logP	0.85	ALOGPS
logP	1.11	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	2.19	ChemAxon
pKa (Strongest Basic)	-8.1	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	91.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	43.87 m³·mol⁻¹	ChemAxon
Polarizability	17.17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	138.598	30932474
DeepCCS	[M-H]-	135.773	30932474
DeepCCS	[M-2H]-	171.915	30932474
DeepCCS	[M+Na]+	147.453	30932474
AllCCS	[M+H]+	143.0	32859911
AllCCS	[M+H-H2O]+	139.3	32859911
AllCCS	[M+NH4]+	146.5	32859911
AllCCS	[M+Na]+	147.5	32859911
AllCCS	[M-H]-	138.0	32859911
AllCCS	[M+Na-2H]-	139.3	32859911
AllCCS	[M+HCOO]-	140.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Chloro-5-methylmaleylacetate	CC(C(O)=O)C(=O)\C=C(\Cl)C(O)=O	2707.2	Standard polar	33892256
2-Chloro-5-methylmaleylacetate	CC(C(O)=O)C(=O)\C=C(\Cl)C(O)=O	1367.1	Standard non polar	33892256
2-Chloro-5-methylmaleylacetate	CC(C(O)=O)C(=O)\C=C(\Cl)C(O)=O	1684.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Chloro-5-methylmaleylacetate,1TMS,isomer #1	CC(C(=O)/C=C(/Cl)C(=O)O)C(=O)O[Si](C)(C)C	1662.1	Semi standard non polar	33892256
2-Chloro-5-methylmaleylacetate,1TMS,isomer #2	CC(C(=O)O)C(=O)/C=C(/Cl)C(=O)O[Si](C)(C)C	1644.9	Semi standard non polar	33892256
2-Chloro-5-methylmaleylacetate,1TMS,isomer #3	CC(C(=O)O)=C(/C=C(/Cl)C(=O)O)O[Si](C)(C)C	1778.0	Semi standard non polar	33892256
2-Chloro-5-methylmaleylacetate,2TMS,isomer #1	CC(C(=O)/C=C(/Cl)C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1731.8	Semi standard non polar	33892256
2-Chloro-5-methylmaleylacetate,2TMS,isomer #2	CC(C(=O)O[Si](C)(C)C)=C(/C=C(/Cl)C(=O)O)O[Si](C)(C)C	1823.0	Semi standard non polar	33892256
2-Chloro-5-methylmaleylacetate,2TMS,isomer #3	CC(C(=O)O)=C(/C=C(/Cl)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1820.8	Semi standard non polar	33892256
2-Chloro-5-methylmaleylacetate,3TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)=C(/C=C(/Cl)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1819.9	Semi standard non polar	33892256
2-Chloro-5-methylmaleylacetate,3TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)=C(/C=C(/Cl)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1745.8	Standard non polar	33892256
2-Chloro-5-methylmaleylacetate,3TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)=C(/C=C(/Cl)C(=O)O[Si](C)(C)C)O[Si](C)(C)C	1870.6	Standard polar	33892256
2-Chloro-5-methylmaleylacetate,1TBDMS,isomer #1	CC(C(=O)/C=C(/Cl)C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	1924.0	Semi standard non polar	33892256
2-Chloro-5-methylmaleylacetate,1TBDMS,isomer #2	CC(C(=O)O)C(=O)/C=C(/Cl)C(=O)O[Si](C)(C)C(C)(C)C	1897.1	Semi standard non polar	33892256
2-Chloro-5-methylmaleylacetate,1TBDMS,isomer #3	CC(C(=O)O)=C(/C=C(/Cl)C(=O)O)O[Si](C)(C)C(C)(C)C	2037.0	Semi standard non polar	33892256
2-Chloro-5-methylmaleylacetate,2TBDMS,isomer #1	CC(C(=O)/C=C(/Cl)C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2182.8	Semi standard non polar	33892256
2-Chloro-5-methylmaleylacetate,2TBDMS,isomer #2	CC(C(=O)O[Si](C)(C)C(C)(C)C)=C(/C=C(/Cl)C(=O)O)O[Si](C)(C)C(C)(C)C	2278.0	Semi standard non polar	33892256
2-Chloro-5-methylmaleylacetate,2TBDMS,isomer #3	CC(C(=O)O)=C(/C=C(/Cl)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2279.0	Semi standard non polar	33892256
2-Chloro-5-methylmaleylacetate,3TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)=C(/C=C(/Cl)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2469.9	Semi standard non polar	33892256
2-Chloro-5-methylmaleylacetate,3TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)=C(/C=C(/Cl)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2312.1	Standard non polar	33892256
2-Chloro-5-methylmaleylacetate,3TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)=C(/C=C(/Cl)C(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2290.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Chloro-5-methylmaleylacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kal-4900000000-c28200bbf22d595a0fb8	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Chloro-5-methylmaleylacetate GC-MS (2 TMS) - 70eV, Positive	splash10-00g0-9262000000-99b176dd5a9c6d212d3a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Chloro-5-methylmaleylacetate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methylmaleylacetate 10V, Positive-QTOF	splash10-0nmr-1910000000-b786b9ed3de776e01530	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methylmaleylacetate 20V, Positive-QTOF	splash10-08fu-4900000000-adbb251eaf55d78de066	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methylmaleylacetate 40V, Positive-QTOF	splash10-0a4i-9200000000-3d748d3233dd20d94d01	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methylmaleylacetate 10V, Negative-QTOF	splash10-0w29-0970000000-9320ad08d2d9c6dbf75e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methylmaleylacetate 20V, Negative-QTOF	splash10-01ox-1900000000-5ec47cde3a13f9fbd02d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methylmaleylacetate 40V, Negative-QTOF	splash10-03di-4900000000-6cc145e9c04fca2a9942	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methylmaleylacetate 10V, Positive-QTOF	splash10-06s9-4910000000-467c3bfde9e1fd05269a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methylmaleylacetate 20V, Positive-QTOF	splash10-0bvi-8900000000-e91cc1669b3a3eec8c12	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methylmaleylacetate 40V, Positive-QTOF	splash10-0bt9-9200000000-dc1e13c96e82651cee93	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methylmaleylacetate 10V, Negative-QTOF	splash10-03di-1920000000-5bba806825843ad1ccda	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methylmaleylacetate 20V, Negative-QTOF	splash10-044i-5900000000-763c871773beab826005	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Chloro-5-methylmaleylacetate 40V, Negative-QTOF	splash10-001i-9200000000-0e699a0180d66ca2eee8	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C18305

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9543299

PDB ID

Not Available

ChEBI ID

81656

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]

Enzymes

Enzyme Details

1. Carboxymethylenebutenolidase homolog

General function:: Involved in hydrolase activity
Specific function:: Cysteine hydrolase. Can convert the prodrug olmesartan medoxomil into its pharmacologically active metabolite olmerstatan, an angiotensin receptor blocker, in liver and intestine. May also activate beta-lactam antibiotics faropenem medoxomil and lenampicillin.
Gene Name:: CMBL
Uniprot ID:: Q96DG6
Molecular weight:: Not Available

Reactions

2-Chloro-5-methyl-cis-dienelactone + Water → 2-Chloro-5-methylmaleylacetate	details

Showing metabocard for 2-Chloro-5-methylmaleylacetate (HMDB0060346)

MOL for HMDB0060346 (2-Chloro-5-methylmaleylacetate)

3D MOL for HMDB0060346 (2-Chloro-5-methylmaleylacetate)

3D SDF for HMDB0060346 (2-Chloro-5-methylmaleylacetate)

3D-SDF for HMDB0060346 (2-Chloro-5-methylmaleylacetate)

PDB for HMDB0060346 (2-Chloro-5-methylmaleylacetate)

3D PDB for HMDB0060346 (2-Chloro-5-methylmaleylacetate)

SMILES for HMDB0060346 (2-Chloro-5-methylmaleylacetate)

INCHI for HMDB0060346 (2-Chloro-5-methylmaleylacetate)

Structure for HMDB0060346 (2-Chloro-5-methylmaleylacetate)

3D Structure for HMDB0060346 (2-Chloro-5-methylmaleylacetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions